Letting them in on the secret

Dear Dave,

I’m in a very fortunate position when it comes to my finances. I’m 25, and I make $50,000 a year. I’m also completely debt-free. In your opinion, when is it appropriate to let someone you’re dating know about your financial situation?

–Anonymous

Dear Anonymous,

Wow, you are in a great position for someone so young. I’m not sure how you got there, but it certainly wasn’t by being dumb or immature.

I think it’s only natural in a dating situation to reveal more about oneself as time passes and the relationship gets deeper and more serious. In my mind, people who start throwing around financial information on a first date are either extremely superficial or just plain weird.

But after you’ve been dating a while, and definitely before you’re engaged, you should know everything about the other person. There should be complete disclosure in every area of your lives. That’s called intimacy. There’s no room for skeletons in the closet when it comes to a healthy relationship.

Just take your time and make sure you’re both committed to being open and honest about things. Then, as the relationship progresses, the depth of intimacy and the depth of information will progress in all areas of your lives.

–Dave

What’s the worst that can happen?

Dear Dave,

My wife and I want to do a live-in/flip real estate purchase. The idea is to buy a fixer-upper and rent out the basement to help with the mortgage payments. What do you think about the idea?

–Brian

Dear Brian,

I love real estate. I’ve flipped a few houses in my day, too. But the particulars of the deal make me a little nervous.

In a situation like this you need to do a basic business analysis. You’ve got to have a plan and figure out the worst case scenario. Part of this is determining whether or not you can survive if things fall apart. In this case, the worst case is that you can’t get a renter and the house doesn’t sell. It puts your family in jeopardy if this happens, so to me it’s not an option.

Honestly, I think you’ve got house fever right now. The possibility I just mentioned isn’t a rare occurrence. Lots of people have had the same idea, with the best of intentions, and still end up in a big mess. But if you and your wife are willing to accept the possibility of things not working out like you planned—and the fact that you might have to take additional jobs for an unknown period of time just to make ends meet—then it might be a play. Me? I don’t like putting myself into skin-of-my-teeth positions intentionally. When I wore a younger man’s clothes, I was willing to do stuff and ignore the risk involved. Going broke years ago knocked that out of me in a hurry. Any deal that runs the risk of leaving you bankrupt, or the victim of a foreclosure, just isn’t worth it!

—Dave

* Dave Ramsey is America’s trusted voice on money and business. He’s authored four New York Times best-selling books: Financial Peace, More Than Enough, The Total Money Makeover and EntreLeadership.The Dave Ramsey Show is heard by more than 5 million listeners each week on more than 500 radio stations. Follow Dave on Twitter at @DaveRamsey and on the web at daveramsey.com.